When The Grass Isn't Greener: Avoiding Career Change Disasters

A friend of mine had a lifelong dream of opening up a coffee shop and was willing to put a highly successful career on the line to pursue it. Fortunately, he was presented with an amazing opportunity to test-drive his grass-is-greener ideal, and the results might surprise you and offer guidance that you can apply to your next big decision.

Dave had it all planned out, even down to the lighting and indie musicians that would be playing on Thursday nights in his vision of the perfect coffeehouse.

ANTONIN THUILLIER/AFP/Getty Images

Then he got an opportunity that most of us don’t have before we make the plunge: He got to learn the ropes working at the best café in Chicago. He immersed himself in coffee culture for a week of training that was nothing short of blissful. Then, he got a chance to put it to work for another few weeks.

His findings? In an average eight-hour day, he got to interact with customers and craft their coffee concoctions for approximately 20 minutes. The remaining seven hours and 40 minutes were spent with dirty dishes. Lots of dirty dishes.

As a result, Dave not only ruled out opening his own coffee shop, but also uncovered a new appreciation for his chosen profession. He wasn’t forced to learn that the grass was not greener in the hardest way possible.

Enjoy hearing Dave tell his own story in this essay on NPR’s All Things Considered by clicking HERE.

Most of us, of course, can’t take off a month of work to test-drive an alternative, but we absolutely can orchestrate a virtual test-drive that will bring into better focus the hue of the alternative arboretum.

You can research ad nauseam online. You can meet with someone who does something close to what you want to do and ask them what they hate about the job. You can calculate the additional education that is required and estimate the lost income that is practically a given in any major career change.

What I’m not talking about is giving up on your dreams and settling for a safer or blander existence. (In fact, if you read more of my posts on career, in particular, I think you’d find that I’m very prooptimizing significance in your life and work.) What I am talking about is being fully informed, researching every angle of your dreams and not filtering out the less attractive elements.

Behavioral scientists, psychologists and economists have done a great deal to educate us on how best to pursue major (as well as minor) life decisions. We need to enlist the help of both parts of our brain. This concept is best articulated by Daniel Kahneman in his book Thinking, Fast and Slow. (Richard Thaler’s new book, Misbehaving, also does a remarkable job of giving an even broader context to the science and psychology that shaped behavioral economics, including Kahneman’s work.)

Kahneman explains how our brains utilize two devices — or systems — to make decisions. The “fast” part of our brain, System 1, is the instinctive part — the feeling, sensing “gut” that drives far more of our decision making than we think. The “slow” part, System 2, is the thinking, deliberate part required to do anything from a complex multiplication problem to juggling all the factors in considering a new job opportunity. System 1 is reflexive, while System 2 is reflective.

If you’re more of a visual learner, like I am, you might appreciate Jonathan Haidt’s zoological metaphor for the two systems. System 1 he describes as an emotional Elephant, and System 2, its educated Rider. The Elephant provides the will to tackle a new endeavor, but the Rider helps ensure that the will is being optimally applied, thereby dramatically increasing our chances of success and better predicting potential failures to avoid.

For Dave, the Elephant was ready to schedule the ribbon cutting at his new craft coffeehouse; thankfully, he enlisted the Rider to gather more information.

This logic applies for many other alternatives in life as well:

The house you found seems like it was built just for you — but anytime you upsize, you must commit to a personal austerity plan for the first six to 18 months. Can you stick to it?

You see the promise of passive income in purchasing a rental property — but have you explored the responsibilities of a landlord and readied yourself for the hassle fixing an over-flowing toilet at 2 in the morning?

You’re financially prepared to retire and ready to inform your boss — but have you tried living off your projected fixed income for a several months? And have you deliberated over what your weeks, months and years will look like beyond choosing flip flops or golf shoes?

A personal trainer has motivated you to follow an aggressive routine to drop 20 pounds — but have you planned for the impact on your grocery shopping and acknowledged the pain in your future so you can fit into that slimmer outfit? (It’s worth it, by the way.)

You bought a beautiful guitar and scheduled lessons to birth your inner musician — but have you scheduled the hour-a-day practice sessions and bought the Band-Aids for the blisters on your fingertips?

Sometimes the grass is greener on the other side, but we need not leave that comparison solely up to fate. By inviting our will and our intellect (our Elephant and our Rider) to join forces, we can test-drive alternate paths in life to help ensure an outcome with a higher probability of delivering the fulfillment we seek.

I’m an advisor, speaker and the author of "Simple Money: A No-Nonsense Guide to Personal Finance." I’m not spouting untested philosophy—I work with clients and advisors as a Wealth Advisor and the Director of Advisor Development for Buckingham Strategic Wealth and the BAM Al...